DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
Response to Amendment
The reply of 22 December 2025 has been entered.
Disposition of claims:
Claims 1-23 are pending.
Response to Arguments
Applicant's arguments filed 22 December 2026 regarding the rejections of claims 1-3, 5-8, and 13-22 are rejected under 35 U.S.C. 103 as being unpatentable over Takada et al. (US 2019/0039996 A1) (hereafter “Takada”) and evidenced by Yi et al. (“Blue Organic Light-Emitting Device Based on Dopant TBP”, 2011 Second International Conference on Digital Manufacturing & Automation, DOI: 10.1109/ICDMA.2011.72 (2011) pp. 271-273.) (hereafter “Yi”) set forth in the last Office action as well as the rejections of claims 10-12 are rejected under 35 U.S.C. 103 as being unpatentable over Takada et al. (US 2019/0039996 A1) (hereafter “Takada”), and further in view of Li et al. (US 2002/0076576 A1) (hereafter “Li”) set forth in the last Office action have been fully considered but they are not persuasive.
Applicant argues that it would not have been obvious over the teachings of Takada. Applicant argues that it would not have been obvious to have selected a lead compound and modify any lead compound to have the structure of the claimed compounds Applicant additionally argues that comparative compounds of Takada teach away from the modifications to produce the claimed compounds.
Takada teaches compounds of similar construction and use to those of the current claims. One of ordinary skill in the art would have been motivated to select a compound from the exemplified compounds of Takada to modify in order to produce additional compounds having the beneficial properties taught by Takada. Specifically, it would have been obvious to modify an exemplified compound of Takada in order to produce additional hole transport materials for beneficial use in organic light emitting devices, i.e. to provide devices having emission efficiency and long lifetime {paragraphs [0083], [0114], [0137]-[0138], and [0168]}.
Takada teaches 24 exemplified compounds selecting one of these compounds for modification is consistent with MPEP 2143. Example 11 of MPEP 2143(I)(B) describes a prior art reference with 18 exemplified compounds. Example 11 states “… and experts had opined that one of ordinary skill in the art would have selected the eighteen compounds to pursue further investigation …”. Example 11 of MPEP 2143(I)(B) further states that “In response to Altana’s argument that the prior art must point to only a single lead compound for further development, the Federal Circuit stated that a "restrictive view of the lead compound test would present a rigid test similar to the teaching-suggestion-motivation test that the Supreme Court explicitly rejected in KSR.” Additionally, Example 1 of MPEP 2143(I)(E) describes that selecting one of 53 options would have been an acceptable number to form a reasonable expectation of success.
Regarding the modification itself, the moiety for substitution is explicitly exemplified by Takada in Compound 24 and in structure Ar-8 of paragraph [0013]. Selecting this option from the limited number of options exemplified by Takada would have been a selection from a finite number of identified, predictable solutions. While the majority of compounds of Takada having the tetraphenylene structure, this does not represent a teaching away of the terphenyl structure. Given the exemplification in 1 of 24 compounds and 1 of ten specific options for the structure of Formula 2 of Takada, the choice of the terphenyl structure would have been a choice from a finite number of identified predictable options.
While Applicant asserts that the Comparative compounds of Takada are closer to the compounds of the current claims, these compounds of Takada lack the features of the disclosure of Takada that would impart the benefits taught by Takada. The Comparative compounds also lack the claimed feature of having a moiety having the structure of the instant formula (2). It does not appear that the Comparative compounds are closer to the current claims that the exemplified inventive compounds of Takada. Additionally, the comparative compounds of Takada do not represent a teaching away from compounds comprising a terphenyl structure as the moiety having the structure of Formula 2 of Takada. The data of Takada does not support Applicant’s assertions given the lack of inventive features. The inventive feature of Takada is present in the compound 19 of Takada.
Applicant's arguments filed 22 December 2026 regarding the rejections of claims 1-3, 5-8, and 13-22 are rejected under 35 U.S.C. 103 as being unpatentable over Takada et al. (US 2019/0039996 A1) (hereafter “Takada”) and evidenced by Yi et al. (“Blue Organic Light-Emitting Device Based on Dopant TBP”, 2011 Second International Conference on Digital Manufacturing & Automation, DOI: 10.1109/ICDMA.2011.72 (2011) pp. 271-273.) (hereafter “Yi”) set forth in the last Office action as well as the rejections of claims 10-12 are rejected under 35 U.S.C. 103 as being unpatentable over Takada et al. (US 2019/0039996 A1) (hereafter “Takada”), and further in view of Li et al. (US 2002/0076576 A1) (hereafter “Li”) set forth in the last Office action have been fully considered but they are not persuasive.
Applicant argues that the proffered results are a showing of unexpected results commensurate in scope with the current claims, rendering the claims nonobvious.
The proffered results do not appear to be commensurate in scope with the current claims. It cannot be determined that the observed improved results due to the chemical compound structural differences alone and are not the consequence of, for example, improved energy level alignment between different layers. Additionally, the observed improved results may be the result of the chemical compound structural differences in combination with a device utilizing multiple hole transport layers.
Declarant’s hypothesis that improved pi-election delocalization in the claimed compounds results in the observed improved device performance has been considered. However, Declarant’s assertion that OLED structures will behave similarly due to the inherent similarity of sandwiching emitting and conduction layers between anodes and cathodes is not persuasive for the reasons described above. Absent further technical reasoning and/or additional data, the arguments are not persuasive and the rejections are maintained.
Applicant's arguments filed 22 December 2026 regarding the rejections of claims 1-2 and 5-9 are rejected under 35 U.S.C. 103 as being unpatentable over Takada et al. (US 2019/0039996 A1) (hereafter “Takada”) set forth in the last Office action have been fully considered but they are not persuasive.
Applicant argues that it would not have been obvious over the teachings of Takada. Applicant argues that it would not have been obvious to have selected a lead compound and modify any lead compound to have the structure of the claimed compounds Applicant additionally argues that comparative compounds of Takada teach away from the modifications to produce the claimed compounds.
Takada teaches compounds of similar construction and use to those of the current claims. One of ordinary skill in the art would have been motivated to select a compound from the exemplified compounds of Takada to modify in order to produce additional compounds having the beneficial properties taught by Takada. Specifically, it would have been obvious to modify an exemplified compound of Takada in order to produce additional hole transport materials for beneficial use in organic light emitting devices, i.e. to provide devices having emission efficiency and long lifetime {paragraphs [0083], [0114], [0137]-[0138], and [0168]}.
Takada teaches 24 exemplified compounds selecting one of these compounds for modification is consistent with MPEP 2143. Example 11 of MPEP 2143(I)(B) describes a prior art reference with 18 exemplified compounds. Example 11 states “… and experts had opined that one of ordinary skill in the art would have selected the eighteen compounds to pursue further investigation …”. Example 11 of MPEP 2143(I)(B) further states that “In response to Altana’s argument that the prior art must point to only a single lead compound for further development, the Federal Circuit stated that a "restrictive view of the lead compound test would present a rigid test similar to the teaching-suggestion-motivation test that the Supreme Court explicitly rejected in KSR.” Additionally, Example 1 of MPEP 2143(I)(E) describes that selecting one of 53 options would have been an acceptable number to form a reasonable expectation of success.
Regarding the modification itself, the moiety for substitution is explicitly exemplified by Takada in Compounds 19 and 20 and in structure Ar-14 of paragraph [0015]. Selecting this option from the limited number of options exemplified by Takada would have been a selection from a finite number of identified, predictable solutions. While the majority of compounds of Takada having the tetraphenylene structure, this does not represent a teaching away of the terphenyl structure. Given the exemplification in 1 of 24 compounds and 1 of 6 specific options for the structure of Ar2 or Ar3 of Takada, the choice of the terphenyl structure would have been a choice from a finite number of identified predictable options.
While Applicant asserts that the Comparative compounds of Takada are closer to the compounds of the current claims, these compounds of Takada lack the features of the disclosure of Takada that would impart the benefits taught by Takada. The Comparative compounds also lack the claimed feature of having a moiety having the structure of the instant formula (2). It does not appear that the Comparative compounds are closer to the current claims that the exemplified inventive compounds of Takada. Additionally, the comparative compounds of Takada do not represent a teaching away from compounds comprising a terphenyl structure as the moiety having the structure of Formula 2 of Takada. The data of Takada does not support Applicant’s assertions given the lack of inventive features. The inventive feature of Takada is present in the compound 2 of Takada.
Applicant's arguments filed 22 December 2026 regarding the rejections of claims 1-2 and 5-9 are rejected under 35 U.S.C. 103 as being unpatentable over Takada et al. (US 2019/0039996 A1) (hereafter “Takada”) set forth in the last Office action have been fully considered but they are not persuasive.
Applicant argues that the proffered results are a showing of unexpected results commensurate in scope with the current claims, rendering the claims nonobvious.
The proffered results do not appear to be commensurate in scope with the current claims. It cannot be determined that the observed improved results due to the chemical compound structural differences alone and are not the consequence of, for example, improved energy level alignment between different layers. Additionally, the observed improved results may be the result of the chemical compound structural differences in combination with a device utilizing multiple hole transport layers.
Declarant’s hypothesis that improved pi-election delocalization in the claimed compounds results in the observed improved device performance has been considered. However, Declarant’s assertion that OLED structures will behave similarly due to the inherent similarity of sandwiching emitting and conduction layers between anodes and cathodes is not persuasive for the reasons described above. Absent further technical reasoning and/or additional data, the arguments are not persuasive and the rejections are maintained.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claim(s) 1-3, 5-8, and 13-23 are rejected under 35 U.S.C. 103 as being unpatentable over Takada et al. (US 2019/0039996 A1) (hereafter “Takada”) and evidenced by Yi et al. (“Blue Organic Light-Emitting Device Based on Dopant TBP”, 2011 Second International Conference on Digital Manufacturing & Automation, DOI: 10.1109/ICDMA.2011.72 (2011) pp. 271-273.) (hereafter “Yi”).
Regarding claims 1-2, 5-8, and 13-14: Takada discloses the compound shown below {(paragraphs [0006] and [0055]: The compounds of the disclosure of Takada have the structure of Formula 1 of Takada.), (paragraph [0082]: The compounds of the disclosure of Takada are exemplified by Compounds 1 through 24.), (p. 23, Compound 19)}.
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Takada teaches that the compounds of Takada are useful as the material for the hole transport layer of an organic electroluminescent device {paragraphs [0025], [0034], [0083], [0087], [0090]-[0091], and [0099]-[0106]}.
The compound shown above does not meet the limitations of the current claim 1, because the quaterphenyl group is not consistent with the aryl group comprising the instant Ar1.
However, Takada teaches that the compounds of Takada have the structure of Formula 1 of Takada (shown below) where at least one of Ar1 to Ar3 is Formula 2 of Takada (shown below) {paragraphs [0006]-[0007] and [0055]-[0058]}.
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Where the index l can be zero {paragraphs [0008] and [0060]}.
This is exemplified by Takada’s structure Ar-8 (shown below) as an example of a moiety meeting the limitations of Takada’s Formula 2 {paragraphs [0013] and [0073]}.
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Thus, the structure Ar-8 of Takada shown above was a known alternative to the quaterphenyl group of the compound of Takada.
At the time the invention was effectively filed, it would have been obvious to have replaced the quaterphenyl group of the compound of Takada shown above with the structure Ar-8 of Takada shown above, based on the teaching of Takada. The substitution would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). The selection of structure Ar-8 of Takada would have been a choice from a finite number of identified, predictable solutions (the exemplified groups having the structure of Formula 2 of Takada), with a reasonable expectation of success. See MPEP 2143(I)(E). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of substituent and substituent positions to be used to make compounds for use in an organic light-emitting device in order to produce optimal organic light emitting devices.
In the resultant compound the instant Ar3 is hydrogen; m is 1; n is 1; and the instant Ar1 has the structure of formula (1-a).
Regarding claim 3: Takada teaches all of the features with respect to claim 1, as outlined above.
The modified compound of Takada does not comprise the instant Ar3 as substituted or unsubstituted phenyl.
However, as outlined above, Takada teaches that the compounds of Takada have the structure of Formula 1 of Takada (shown below) where at least one of Ar1 to Ar3 is Formula 2 of Takada {paragraphs [0006]-[0007] and [0055]-[0058]}.
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In the modified compound of Takada shown above, each of L1 to L3 can be equated with phenylene and Ar3 of Takada can be equated with phenyl. Takada teaches that each of Ar3 of Takada can be biphenyl in addition to phenyl {paragraphs [0014], [0032], [0061], [0071], and [0075]}.
At the time the invention was effectively filed, it would have been obvious to have replaced the phenyl group that can be equated with the group Ar3 of the compound of Takada shown above with biphenyl, based on the teaching of Takada. The substitution would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). The selection of biphenyl would have been a choice from a finite number of identified, predictable solutions (the described options for Ar3 of Takada), with a reasonable expectation of success. See MPEP 2143(I)(E). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of substituent and substituent positions to be used to make compounds for use in an organic light-emitting device in order to produce optimal organic light emitting devices.
Regarding claims 15-23: Takada teaches all of the features with respect to claim 1, as outlined above.
Takada does not exemplify a specific organic electroluminescent device comprising the modified compound of Takada described above.
However, Takada teaches that the compounds of Takada are useful as the material for the hole transport layer of an organic electroluminescent device {paragraphs [0025], [0034], [0083], [0087], [0090]-[0091], and [0099]-[0106]}.
Takada additionally teaches the structure of an organic electroluminescent device comprising a cathode, an anode, and organic layers intervening between the cathode and the anode and exemplifies such a structure in the examples {paragraphs [0084]-[0087] and Fig. 2 as well as the structure of the example devices described in paragraphs [0157]-[0160]}. The organic layer comprises a light emitting layer and a hole transporting zone between the anode and the light emitting layer {paragraphs [0101]-[0106] as well as the structure of the example devices described in paragraphs [0157]-[0160]}. The hole transporting zone comprises a first hole transporting layer on the anode side and a second hole transporting layer on the cathode side {paragraphs [0101]-[0106] as well as the structure of the example devices described in paragraphs [0157]-[0160]}. The light emitting layer and the second hole transporting layer are in direct contact with each other {paragraphs [0101]-[0106] as well as the structure of the example devices described in paragraphs [0157]-[0160]}.
The second hole transport layer comprises the compound of the disclosure of Takada {paragraphs [0101]-[0106] as well as the structure of the example devices described in paragraphs [0157]-[0160]}.
The total thickness of the first hole transporting layer and the second hole transporting layer is 120 nm {The structure of the example devices described in paragraphs [0157]-[0160]}.
The first hole transporting layer comprises TNATA, which has the structure shown below {The structure of the example devices described in paragraphs [0157]-[0160]}.
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The emitting layer is a single layer comprising a light emitting compound—TBP—exhibiting fluorescence emission {The structure of the example devices described in paragraphs [0157]-[0160]}. Yi provides evidence that TBP exhibits fluorescence emission with a main peak wavelength less than 500 nm {p. 273, 1st col., 2nd and 3rd paragraphs}.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have further modified the compound of Takada by using the compound as the material of the second hole transporting layer of the device structure of Takada described above, based on the teaching of Takada. The modification would have been a combination of prior art elements according to known methods to yield predictable results. See MPEP 2143(I)(A). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of materials to be used to make an organic light-emitting device in order to produce optimal organic light-emitting devices.
TNATA has the structure of the instant formula (21) where LA1, LB1, and LC1 are single bonds and A1, B1, and C1 are each substituted phenyl.
Claim(s) 10-12 are rejected under 35 U.S.C. 103 as being unpatentable over Takada et al. (US 2019/0039996 A1) (hereafter “Takada”) as applied to claim 1 above, and further in view of Li et al. (US 2002/0076576 A1) (hereafter “Li”).
Regarding claims 10-12: Takada teaches all of the features with respect to claim 1, as outlined above.
The modified compound of Takada does not comprise any deuterium atoms.
Li teaches organic light-emitting electronic devices containing conjugated material wherein one or more hydrogens have been replaced with deuterium {abstract}. Li teaches that when deuterium is substituted for hydrogen on organic semiconductors compounds, the deuterated compounds possess improved thermal stability and longer lifetime in optoelectronic devices due to the stronger nature of the C-D bond relative to the C-H bond {p. 2, ¶ [0009], lines 11-13}. Li teaches that the compounds can be fully deuterated {paragraphs [0025] and [0027]-[0028]}.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have further modified the compound of Takada such that the compound of Takada was fully deuterated, based on the teaching of Li. One of ordinary skill in the art would have been motivated to use materials that provide increased lifetime for the organic electroluminescent devices in which they’re used, based on the teachings of Li. Furthermore, one of ordinary skill in the art would have been motivated to maximize the number of C-D bonds in order to maximize the thermal stability of the compound to produce a fully deuterated compound, as taught by Li.
Claim(s) 1-2 and 5-9 are rejected under 35 U.S.C. 103 as being unpatentable over Takada et al. (US 2019/0039996 A1) (hereafter “Takada”).
Regarding claims 1-2 and 5-9: Takada discloses the compound shown below {(paragraphs [0006] and [0055]: The compounds of the disclosure of Takada have the structure of Formula 1 of Takada.), (paragraph [0082]: The compounds of the disclosure of Takada are exemplified by Compounds 1 through 24.), (p. 20, Compound 2)}.
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The compound shown above does not meet the limitations of the current claim 1, because the moiety comprising the naphthyl group is not consistent with the limitations of the optional substituents of the instant formula (2)—the instant R45 cannot be phenyl.
However, Takada teaches that the compounds of Takada have the structure of Formula 1 of Takada (shown below) where at least one of Ar1 to Ar3 is Formula 2 of Takada (shown below) {paragraphs [0006]-[0007] and [0055]-[0058]}.
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Where the index l can be zero {paragraphs [0008] and [0060]}. This is exemplified by Takada’s structures Ar-8 and Ar-9 as examples moieties meeting the limitations of Takada’s Formula 2 {paragraphs [0013] and [0073]}.
Thus, a compound similar to the compound of Takada shown above except for having l of Formula 2 of Takada would have been a known variation of the compound of Takada.
At the time the invention was effectively filed, it would have been obvious to have modified the compound of Takada by using a structure consistent with Takada’s Formula 2 where l is 0, which would result in a structure
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, based on the teaching of Takada. The modification would have been a combination of prior art elements according to known methods to yield predictable results. See MPEP 2143(I)(A). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of substituent and substituent positions to be used to make compounds for use in an organic light-emitting device in order to produce optimal organic light emitting devices.
The resultant monoamine compound would comprise one group on the central N atom having the structure of the instant formula (2) and an additional two groups on the central N atom that are biphenyl groups. The instant Ar3 is hydrogen; m is 0 and n is 1 or m is 1 and n is 0; Ar1 has the structure of the instant formula (1-a).
Allowable Subject Matter
Claim 4 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter: As outlined above, Takada is the closest prior art. While the teachings of Takada encompass the case where the instant Ar3 is a substituted or unsubstituted naphthyl, the number of modifications required to an exemplified compound or the number of choice necessary based on the structural formulas of Takada alone would not represent a finite number of identified, predictable solutions with a reasonable expectation of success. The broader prior art does not provide teachings that would teach or motivate the required number of modifications and/or choices.
Conclusion
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DYLAN CLAY KERSHNER whose telephone number is (303)297-4257. The examiner can normally be reached M-F, 9am-5pm (Mountain).
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/DYLAN C KERSHNER/Primary Examiner, Art Unit 1786
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